Ryan Holiday’s The Obstacle Is the Way: A Toolbox for Success - The Objective Standard
Obstacle Is the Way

The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph, by Ryan Holiday. New York: Penguin Group, 2014. 201 pp. $15.78 (hardcover).

Perhaps your boss has ignored ideas for increasing sales or reducing costs, or maybe you want to become a professional speaker but have a poor voice or a speech impediment that’s blocking the way, or perhaps you’re having trouble meeting the right girl or guy for romance. Whatever obstacles you face, Ryan Holiday’s The Obstacle Is the Way can provide you with lessons not only for overcoming them, but also for using them as a means to success.

The book’s title is a paraphrase of a maxim from the Stoic philosopher and Roman emperor, Marcus Aurelius, who said, “The impediment to action advances action. What stands in the way becomes the way.”

In practice, this could mean that if your manager ignores your ideas for improving the company, this is the path to starting your own business in which to implement those ideas. It could mean that if you want to become a professional communicator, but a speech impediment hinders your success, this is the way to becoming a successful author. If you are having trouble finding a good romantic partner in all the usual places, this is the road to discovering other places, where more suitable people can be found. And so on. The obstacle is the way.

The book illustrates its points with stories from business, literature, and history. Consider:

Amelia Earhart wanted to be a great aviator. But it was the 1920s, and people still thought that women were frail and weak and didn’t have the stuff. Woman suffrage was not even a decade old.

She couldn’t make her living as a pilot, so she took a job as a social worker. Then one day the phone rang. The man on the line had a pretty offensive proposition, along the lines of: We have someone willing to fund the first female transatlantic flight. Our first choice has already backed out. You won’t get to actually fly the plane, and we’re going to send two men along as chaperones and guess what, we’ll pay them a lot of money and you won’t get anything. Oh, and you very well might die while doing it.

You know what she said to that offer? She said yes.

Because that’s what people who defy the odds do. That’s how people who become great at things—whether it’s flying or blowing through gender stereotypes—do. They start. (p. 71)

In his first chapter, “Live in the Present Moment,” Holiday presents an interesting fact: Dozens of America’s greatest and most enduring companies started during a depression or economic crisis. For example, FedEx opened during the oil crisis of 1973. The owners of these companies

didn’t know whether it would get better or worse, they just knew what was. They had a job they wanted to do, a great idea they believed in or a product they thought they could sell. . . . Yet in our own lives, we aren’t content to deal with things as they happen. We have to dive endlessly into what everything “means,” whether something is “fair” or not . . . and what everyone else is doing. (p. 46) . . .

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